Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | Ethyl chloroformate | HCID 10928 | — |
| Reactant | O-Benzylhydroxylamine | HCID 102313 | — |
| Reactant | HCID 18781934 | HCID 18781934 | — |
| Solvent | Chloroform | HCID 6212 | — |
| Product | HCID 18781932 | HCID 18781932 | 22% |
Reaction Steps
Triethylamine (2 ml) was added to a solution of (4-methylthio-2-oxo-azetidin-1-yl)acetic acid (1.67 g) in dry chloroform (15 ml) cooled to -10° C. After 5 mins ethyl chloroformate (1.6 ml) was added, then after a further 5 mins a solution of O-benzylhydroxylamine free base (1.67 g) in chloroform was added. The solution was allowed to warm to room temperature and stirred for 16 hours then washed with brine, dried (MgSO4) and evaporated. Chromatography of the residue on silica gel (petroleun ether/ethyl acetate) gave N-benzyloxy-(4-methylthio-2-oxo-azetidin-1-yl)acetamide as a clear gum (22% yield).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US06071899 |
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| Source dataset | uspto-grants-2000_06 |
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| ORD ID | ord-ffeaae135f7f41008a5e966d2b0eec24 |
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| Source note | uspto-grants-2000_06 |
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